US4231759A - Liquid hydrocarbon fuels containing high molecular weight Mannich bases - Google Patents
Liquid hydrocarbon fuels containing high molecular weight Mannich bases Download PDFInfo
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- US4231759A US4231759A US05/340,016 US34001673A US4231759A US 4231759 A US4231759 A US 4231759A US 34001673 A US34001673 A US 34001673A US 4231759 A US4231759 A US 4231759A
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- liquid hydrocarbon
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
Definitions
- Typical hydrocarbon fuels boiling in the gasoline range and intended for the use in spark-ignition internal combustion engines which power most automotive units, contain components which possess limited volatility or solubility in the fuels. In practice such components tend to form deposits in the fuel carburetion system where fuel vaporization occurs. Deposit accumulations on carburetor throttle bodies and plates and intake valves lead to progressively poorer engine performance. Poor performance is exhibited to the operator most noticeably as improper or rough idling of the engine. Less noticeable by the operator is the excessive consumption of fuel and, least of all, the increased level of hydrocarbons and partially burned fuel components in the exhaust gas. Means for preventing or eliminating deposits in carburetor and intake valve systems thus contribute significantly not only to automotive efficiency and economy of operation but also to minimizing pollution of the environment.
- Accumulated deposits may be removed periodically by physical cleaning during engine overhaul or tune-up.
- a preferred solution to the deposits problem requires no interruption of engine usage and this is usually accomplished in practice by inclusion of a carburetor detergent additive in the gasoline fuel.
- Detergents employed for this purpose are not completely effective but have reduced the severity of the problem.
- Carburetor detergent additives must be soluble in the hydrocarbon fuel composition and possess a suitable balance of lyophilic and hydrophilic properties.
- Carburetor detergents of the art while generally alleviating the deposits problem, have exhibited hydrophilic surface-active properties to such a degree that water suspension (haze) and dispersion (emulsion) occur.
- haze water suspension
- dispersion emulsion
- Suitable detergent additives for use in automotive fuels must be capable of keeping intake valves clean.
- a suitable intake valve detergent additive for automotive systems effective in removing and preventing deposits in the intake system while exhibiting no undesirable effects upon other properties of the hydrocarbon fuel.
- a suitable detergent additive for use in gasoline range hydrocarbon fuel will provide and maintain a high degree of cleanliness in both carburetor and intake systems.
- One effective polar grouping suitable for inclusion in oil-soluble surface-active agents is the basic amine grouping, most often as a polyamine and preferably as a polyalkylene polyamine.
- One suitable non-polar grouping for such agents is the alkaryl group usually provided by alkylation of benzene, naphthalene, phenol or homologs thereof.
- Such polar and non-polar groups may be conveniently brought together in one molecular by the well-known Mannich condensation reaction involving an alkyl phenol, a low moleular weight aldehyde and a polyamine.
- Mannich condensation reactions usually proceed with the formation of polymeric resinous products, either by linear growth due to the use of mono-substituted phenols, by polysubstitution on primary amine groups, or by substitution on secondary amine groups of the polyamine. Cross-linking is also possible when an unsubstituted phenol or naphthol is used or when the condensation reaction is forced by the use of catalysts, high reaction temperature, or both. Excess aldehyde may also react with amine groups to form imines or hydroxymethylamines. Accordingly, the properties of such polymeric compositions have principally been utilized in heavier fuels such as heater and furnace oils, as described in U.S. Pat. No. 2,962,442, and in lubricating oils, as disclosed in U.S. Pat. Nos. 3,036,003 and 3,539,633. None of these uses involves a sensitive carburetion system as is found in the gasoline-powered spark-ignition internal combustion system.
- Polymeric Mannich condensation products have often been employed as stabilizers, or anti-oxidants, as well as dispersants, or detergents, in heavy hydrocarbon stocks. Use in lighter hydrocarbon stocks such as gasolines, has been discloed in U.S. Pat. Nos. 3,269,810 and 3,649,229.
- U.S. Pat. No. 3,235,484 (Now U.S. Pat. No. Re. 26,330) describes the addition of certain disclosed compositions to refinery hydrocarbon fuel stocks for the purpose of inhibiting the accumulation of carbonaceous deposits in refinery cracking units.
- the primary inhibitors disclosed are mixtures of amides, imides and amine salts formed by reacting an ethylene polyamine with hydrocarbon substituted succinic acids or anhydride, whose hydrocarbon substituent has at least about 50 carbon atoms.
- U.S. Pat. No. 3,368,972 describes as dispersant-detergent addition agents for lubricating oils high molecular weight Mannich condensation products from (1) high molecular weight alkyl-substituted hydroxyaromatic compounds whose alkyl-substituent has a molecular weight in the range of 600-3000, (2) a compound containing at least one HN ⁇ group and (3) an aldehyde in the respective molar ratio of 1.0:0.1-10:1.0-10.
- the high molecular weight Mannich condensation products of either U.S. Pat. No. 3,235,484 or U.S. Pat. No. 3,368,972 have a drawback in their large-scale preparation and in their extended service used as lubricant addition agents used under high temperature conditions such as encountered in diesel engines.
- the resulting oil concentrate solution of the condensation product either has or develops during storage a haze which is believed to be caused by undissolved or border-line soluble by-products which not only are not substantially incapable of removal by filtration but also severely resrict product filtration rate.
- piston ring groove carbonaceous deposits and skirt varnish tend to build up sufficiently rapidly and prevent desirable long in-service use of such lubricant oils.
- This invention pertains to improved gasoline hydrocarbon fuels containing a detergent additive capable of substantially removing and preventing buildup of deposits on carburetor surfaces and intake valve systems in a gasoline-powered engine system.
- a liquid hydrocarbon combustion fuel containing an amount sufficient to impart improved detergency and antirust properties thereto of an additive composition
- an additive composition comprising the Mannich condensation product of (1) a high molecular weight alkyl-substituted hydroxy-aromatic compound wherein said alkyl has a molecular weight of from about 600 to about 3,000, (2) an amine which contains an HN ⁇ group and, (3) an aldehyde, wherein the respective molar ratio of reactants is 1:0.1-10:0.1-10.
- the Mannich condensation product may be employed alone where carburetor cleanliness is desired or in combination with a suitable essentially non-volatile hydrocarbon as a carrier fluid where intake valve cleanliness is also desired.
- This invention relates to a liquid hydrocarbon combustion fuel containing an amount sufficient to impart improved detergency properties thereto of an additive composition
- an additive composition comprising the condensation product of a high molecular weight alkyl-substituted hydroxyaromatic compound, an amine which contains an amino group having at least one active hydrogen atom, and an aldehyde.
- condensation products can be prepared by condensing in the usual manner under Mannich reaction conditions:
- an alkyl-substituted hydroxyaromatic compound whose alkyl-substituent has a 600-100,000 Mn, preferably a polyalkylphenol whose polyalkyl substituent is derived from 1-mono-olefin polymers having a Mn of about 600-3000, more preferably about 750-1200;
- an amine containing at least one >NH group preferably an alkylene polyamine of the formula ##STR1## wherein A is a divalent alkylene radical having 2 to 6 carbon atoms and x is an integer from 1 to 10; and
- the foregoing high molecular weight products employed in the fuels of this invention are preferably prepared according to the conventional methods heretofore employed for the preparation of Mannich condensation products, using the above-named reactants in the respective molar ratios of high molecular weight alkyl-substituted hydroxyaromatic compound, amine and aldehyde of approximately 1.0:0.1-10:0.1-10.
- a suitable condensation procedure involves adding at a temperature of from room temperature to about 200° F. the formaldehyde reagent (e.g.
- the preferred detergent additives employed in this invention are high molecular weight Mannich condensation products, formed by reacting (1) an alkylphenol, whose alkyl group has 600-3,000 Mn; (2) an ethylene polyamine, an amine reactant; and (3) a formaldehyde-affording reactant in the respective molar ratio of 1.0:0.5-2.0:1.0-3.0.
- high molecular weight alkyl-substituted hydroxyaromatic compounds are polypropylphenol, polybutylphenol and other polyalkylphenols. These polyalkylphenols may be obtained by the alkylation, in the presence of an alkylating catalyst, such as BF 3 , of phenol with high molecular weight polypropylene, polybutylene and other polyalkylene compounds to give alkyl substituents on the benzene ring of phenol having an average 600-100,000 Mn.
- an alkylating catalyst such as BF 3
- the 600 Mn and higher Mn alkyl-substituents on the hydroxyaromatic compounds may be derived from high molecular weight polypropylenes, polybutenes and other polymers of mono-olefins, principally 1-mono-olefins. Also useful are copolymers of mono-olefins with monomers copolymerizable therewith wherein the copolymer molecular contains at least 90%, by weight, of mono-olefin units.
- copolymers of butenes (butene-1, butene-2 and isobutylene) with monomers copolymerizable therewith wherein the copolymer molecule contains at least 90% by weight, of propylene and butene units, respectively.
- Said monomers copolymerizable with propylene or said butenes include monomers containing a small proportion of unreactive polar groups such as chloro, bromo, keto, ether, aldehyde, which do appreciably lower the oil-solubility of the polymer.
- the comonomers polymerized with propylene or said butenes may be aliphatic and can also contain non-aliphatic groups, e.g., styrene, methylstyrene, p-dimethylstyrene, divinyl benzene and the like. From the foregoing limitation placed on the monomer copolymerized with propylene or said butenes, it is abundantly clear that said polymers and copolymers of propylene and said butenes are substantially aliphatic hydrocarbon polymers. Thus the resulting alkylated phenols contain substantially alkyl hydrocarbon substituents having Mn upward from 600.
- others which may be used include, exclusive of sulfurized derivatives, high molecular weight alkyl-substituted derivatives of resorcinol, hydroquinone, cresol, catechol, xylenol, hydroxy diphenyl, benzylphenol, phenethylphenol, naphthol, tolynaphthol, among others.
- Preferred for the preparation of such preferred Mannich condensation products are the polyalkylphenol reactants, e.g., polypropylphenol and polybutylphenol whose alkyl group has a number average molecular weight of 600-3000, the more preferred alkyl groups having a number average molecular weight of 740-1200, while the most preferred alkyl groups is a polypropyl group having a number average molecular weight of 800-850, desirably about 825.
- polyalkylphenol reactants e.g., polypropylphenol and polybutylphenol whose alkyl group has a number average molecular weight of 600-3000, the more preferred alkyl groups having a number average molecular weight of 740-1200, while the most preferred alkyl groups is a polypropyl group having a number average molecular weight of 800-850, desirably about 825.
- alkyl-substituted hydroxyaromatic compound is that of a para-substituted mono-alkylphenol.
- any alkylphenol readily reactive in the Mannich condensation reaction may be employed. Accordingly, ortho mono-alkylphenols and dialkylphenols are suitable for use in this invention.
- Representative amine reactants are alkylene polyamines, principally polyethylene polyamines.
- Other representative organic compounds containing at least one HN ⁇ group suitable for use in the preparation of Mannich condensation products are well known and include the mono and di-amino alkanes and their substituted analogs, e.g., ethylamine, dimethylamine, dimethylaminopropyl amine and diethanol amine; aromatic diamines, e.g., phenylene diamine, diamino naphthalenes; heterocyclic amines, e.g., morpholine, pyrrole, pyrrolidine, imidazole, imidazolidine, and piperidine; melamine and their substituted analogs.
- Suitable alkylene polyamine reactants include ethylenediamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, heptaethylene octamine, octaethylene nonamine, nonaethylene decamine, decaethylene undecamine and mixtures of such amines having nitrogen contents corresponding to the alkylene polyamines, in the formula H 2 N--(A--NH--) n H, mentioned before, where A is divalent ethylene and n is an integer from 1 to 10.
- propylene polyamines such as propylene diamine and di-, tri-, tetra-, penta-propylene tri-, tetra-, penta- and hexa- amines are also suitable reactants.
- the alkylene polyamines are usually obtained by the reaction of ammonia and dihalo alkanes, such as dichloro alkanes.
- the alkylene polyamines obtained from the reaction of 2 to 11 moles of ammonia with 1 to 10 moles of dichloro alkanes having 2 to 6 carbon atoms and the chlorines on different carbons are suitable alkylene polyamine reactants.
- aldehydes for use in the preparation of the high molecular products of this invention include the aliphatic aldehydes such as formaldehyde (including paraformaldehyde and Formalin), acetaldehyde and aldol (b-hydroxybutyraldehyde).
- formaldehyde including paraformaldehyde and Formalin
- acetaldehyde acetaldehyde
- aldol b-hydroxybutyraldehyde
- formaldehyde or a formaldehyde-yielding reactant a formaldehyde-yielding reactant.
- Such detergent compositions may be employed effectively in any liquid hydrocarbon combustion fuel, preferably any gasoline base stock intended for use in spark-ignition internal combustion engines.
- the stock may be predominantly aliphatic or aromatic in character and may contain hydrocarbon components boiling within the range from about 50° F. to about 430° F., derived variously from cracking, reforming, alkylation, polymerization and distillation operations conventionally employed in a petroleum refinery.
- the gasoline may additionally contain butanes for vapor pressure control, metal alkyls for octane improvement, and various additives to minimize oxidation, gas formation, icing in fuel lines or intake systems, and the like.
- PTB bbls.
- Use of a gasoline fuel composition containing our detergent composition at the above concentration levels will also serve to maintain carburetor surfaces and intake valve systems in an especially clean condition.
- the carrier fluid may be used together with the Mannich condensation product already described, particularly where cleanliness in the intake valve system is to be achieved or maintained, may be any suitable hydrocarbon oil which is substantially non-volatile and possesses a viscosity at operating conditions no greater than that of a suitable lubricating oil.
- the carrier fluid may be, for example, a mineral oil fraction or an olefin polymer. Suitable mineral oils include the various solvent-extracted and/or hydrogen-treated lubricating oil fractions, particularly the SAE 40 oils. Suitable olefin polymers, while not so limited, are suitably the same polymers employed in the alkylation of phenolic materials for use in the Mannich condensation product of this invention.
- Other suitable carrier fluids include the alkylated phenolic compounds described above and may also include polyalkylphenols not suitable for Mannich condensation reactions such as trialkyl phenols.
- Polyolefin carrier fluids should have number average molecular weights within the range from about 600 to about 3,000, preferably about 600 to about 1,400 (about 40-100 carbon atoms).
- Especially preferred carrier fluids include polybutene, having Mn of about 900, and polypropylene, having Mn of about 850.
- carrier fluid Whenever carrier fluid is employed, it may be added in any amount up to about 800 wt. %, based on Mannich product (40% active), and the amount added will usually depend upon the concentration of Mannich product employed. For example, at low concentrations of Mannich product where only carburetor cleanliness is of concern, little or no carrier fluid is required. However, at the higher dosages of Mannich product used to achieve intake valve cleanliness as well as a higher weight ratio of carrier fluid is to be preferred. In illustration of this relationship; where 5-20 PTB of Mannich product (40% active) is employed to achieve and maintain carburetor cleanliness, no carrier fluid other than the polyolefin already present in the Mannich product (unreacted during alkylation of phenol prior to the Mannich reaction) is required.
- Mannich condensation product alone or in combination with carrier fluid it is desirable to dilute the material with a light hydrocarbon solvent.
- An aromatic hydrocarbon such as a C 9 mixture of trimethyl benzene and ethyl toluene or propyl benzene, is preferred because of its solvency power and compatibility with gasoline fuels.
- Mannich condensation products were prepared by the reaction of selected alkylphenols and alkylene polyamines with aqueous formaldehyde substantially according to the following generalized procedure.
- a mixture of X moles of alkylphenol and Y moles of amine heated to about 180°-200° F., was charged Z moles of aqueous formaldehyde over a period of 30 minutes while maintaining the temperature of the mixture below 200° F.
- the mixture temperature was maintained at 180°-200° F. with stirring for an additional 30 minutes.
- Xylene solvent was optionally added.
- the reaction mixture was then heated to 300°-350° F. and held at the elevated temperature for 2 hours while blowing with an inert gas to assure removal of all water.
- the reaction product was then cooled filtered and diluted with xylene to provide a concentration level of 40-50 wt. % active Mannich product.
- MS test fuel is a certified gasoline, blended by Amoco Oil Company, used by automotive-associated industries as a reference fuel for the testing of fuel and lubricant additives in spark-ignition internal combustion engines.
- MS-08 contains 0.008 wt. % sulfur.
- Mannich-type dispersants prepared as described in Example I and in combination with carrier fluids were evaluated as detergents for intake systems, employing MS-08 fuel and a 1967 Chevrolet 6-cylinder, 250 CID engine operated to simulate taxicab service using sequences of the following test cycle for 20 hours.
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Abstract
Description
TABLE I __________________________________________________________________________ Experiment Alkyl Phenol Amine Formaldehyde Number Alkyl group (MW) Moles (X) Diamine Moles (Y) Moles (Z) __________________________________________________________________________ 1 Polybutyl (1500) 1 Tetraethylene 1 2 Pentamine 2 Polybutyl (1500) 1 Pentaethylene 2 2 Hexamine 3 Polybutyl (900) 1 Ethylene Diamine 1 3 4 Polybutyl (900) 1 Diethylene 1 3 Triamine 5 Polybutyl (900) 1 Aminoethyl 2 2 Aminoethanol 6 Polybutyl (350) 1 Ethylene Diamine 1 1 7 Polybutyl (250) 1 Aminoethyl 1 1 Aminoethanol 8 Polypropyl (850) 1 Diethylene 1 3 Triamine 9 Polypropyl (600) 1 Diethylene 1 3 Triamine __________________________________________________________________________
______________________________________ Idle High Speed ______________________________________ Cycle Time (min.) 2.75 0.25 Speed (rpm) 525 ± 25 1500 ± 20 Load (bhp) 0 55-60 Coolant temp. (° F.) 195 ± 5 -- Carburetor air temp. (° F.) 160 ± 5 -- Air Humidity 80 ± 5 80 ± 5 Carburetor air press. +0.5 ± 0.03 -7 ± 2 (in. H.sub.2 O) Blowby rate to carburetor 1.0 4.0 ± 2.0 intake (Cfm) Air-fuel ratio 13.0-13.5 -- Mainfold vacuum (in. Hg.) 17 ± 1.5 -- Distributer Vacuum 0.10 ± 0.05 11 ± 1.0 (in. Hg.) Exhaust back press. 1.5 ± 1.0 4.0 ± 1.0 (in. H.sub.2 O) ______________________________________
TABLE II ______________________________________ Manich Product Deposit Weight, Cleanliness Experiment No. PTB mg. (10 = Clean) ______________________________________ 1 3 5.7 8.4 1 6 6.0 9.4 2 6 7.8 9.2 4 6 2.2 9.7 5 6 6.9 9.2 6 6 12.0 8.8 7 6 6.9 8.5 Base Fuel 19.5 6.7 ______________________________________
______________________________________ Cycle Time RPM Load, bhp ______________________________________ I (Idling) 20 sec. 550 0 II (Acceleration) 10 sec. 2,000 52 III (Cruising) 90 sec. 1,500 18 ______________________________________
TABLE III ______________________________________ Mannich Product* Exper- Cleanliness Ratings iment Carrier Fluid Intake Intake No. PTB Oil PTB Value Manifold ______________________________________ 3 40 SAE 40 260 9.0 9.6 4 40 -- -- 6.7 8.9 4 40 SAE 40 130 8.6 9.9 4 40 SAE 40 260 9.3 9.7 4 40 Polybutene (900) 130 9.5 9.5 4 40 Polypropylene (850) 130 9.5 9.5 4 30 Polypropylene (850) 130 9.3 -- 4 20 Polypropylene (850) 130 8.6 9.5 4 20 Polypropyl (850) 130 7.6 9.2 phenol 4 20 Polybutyl (900) 130 7.1 8.9 phenol 8 40 SAE 40 260 9.1 9.7 8 40 Polypropylene (850) 130 9.6 9.5 9 40 SAE 40 260 8.5 9.7 Base 5.9 8.2 Fuel ______________________________________ *100% Active
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Cited By (145)
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US4490155A (en) * | 1983-08-17 | 1984-12-25 | Texaco Inc. | Mannich reaction products of diaminopropanes with formaldehyde and salicyclic acids |
US4508541A (en) * | 1983-07-05 | 1985-04-02 | Texaco Inc. | Mannich reaction product and a motor fuel composition containing same |
EP0178960A1 (en) * | 1984-10-15 | 1986-04-23 | Ethyl Petroleum Additives, Inc. | Diesel fuel compositions |
US4787996A (en) * | 1986-05-21 | 1988-11-29 | Mobil Oil Corporation | Mannich base oil additives |
EP0357311A2 (en) * | 1988-09-02 | 1990-03-07 | Texaco Development Corporation | Motor fuel additive and ori-inhibited motor fuel composition |
WO1990010051A1 (en) * | 1989-02-21 | 1990-09-07 | Union Oil Company Of California | Fuel composition for control of intake valve deposits |
EP0534551A1 (en) * | 1991-09-23 | 1993-03-31 | Shell Internationale Researchmaatschappij B.V. | Gasoline composition |
US5300701A (en) * | 1992-12-28 | 1994-04-05 | Chevron Research And Technology Company | Process for the preparation of polyisobutyl hydroxyaromatics |
US5306313A (en) * | 1988-02-29 | 1994-04-26 | Exxon Chemical Patents Inc. | Dispersant additive comprising the reaction product of a polyanhydride and a mannich condensation product |
WO1994014929A1 (en) | 1992-12-28 | 1994-07-07 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Fuel additive compositions containing aliphatic amines and polyalkyl hydroxyaromatics |
US5352251A (en) * | 1993-03-30 | 1994-10-04 | Shell Oil Company | Fuel compositions |
US5380345A (en) * | 1993-12-03 | 1995-01-10 | Chevron Research And Technology Company | Polyalkyl nitro and amino aromatic esters and fuel compositions containing the same |
US5387266A (en) * | 1993-06-11 | 1995-02-07 | Ethyl Corporation | Mannich base derivatives, and the production and uses thereof |
US5399178A (en) * | 1993-12-17 | 1995-03-21 | Chevron Chemical Company | Mannich condensation products of polyalkylene hydroxyaromatic esters and fuel compositions containing the same |
US5413615A (en) * | 1994-05-02 | 1995-05-09 | Chevron Chemical Company | Polyalkyl hydroxy and amino aromatic carbamates and fuel compositions containing the same |
US5413614A (en) * | 1994-05-02 | 1995-05-09 | Chevron Chemical Company | Mannich condensation products of poly(oxyalkylene) hydroxyaromatic carbamates and fuel compositions containing the same |
WO1995012648A1 (en) * | 1993-11-01 | 1995-05-11 | Ethyl Petroleum Additives Limited | Compositions for control of induction system deposits in internal combustion engines |
WO1995018197A1 (en) * | 1993-12-30 | 1995-07-06 | Chevron Chemical Company | Mannich condensation products of poly(oxyalkylene) hydroxyaromatic esters and fuel compositions containing the same |
US5458661A (en) * | 1994-09-19 | 1995-10-17 | Shell Oil Company | Fuel compositions |
US5458660A (en) * | 1994-09-19 | 1995-10-17 | Shell Oil Company | Fuel compositions |
US5462567A (en) * | 1992-12-28 | 1995-10-31 | Chevron Chemical Company | Fuel additive compositions containing poly(oxyalkylene)hydroxyaromatic esters and aliphatic amines |
US5466268A (en) * | 1994-12-30 | 1995-11-14 | Chevron Chemical Company | Polyalkyl and polyalkenyl aromatic amides and fuel compositions containing the same |
EP0683220A2 (en) | 1994-05-18 | 1995-11-22 | Ethyl Corporation | Lubricant additive compositions |
US5482523A (en) * | 1994-11-02 | 1996-01-09 | Chevron Chemical Company | Mannich condensation products of poly(oxyalkylene) hydroxyaromatic ethers and fuel compositions containing the same |
US5489315A (en) * | 1994-09-19 | 1996-02-06 | Shell Oil Company | Fuel compositions comprising hydantoin-containing polyether alcohol additives |
US5492998A (en) * | 1992-09-08 | 1996-02-20 | Lifesource International, Ltd. | Cross-linked tertiary-amine polymers |
US5503644A (en) * | 1991-09-23 | 1996-04-02 | Shell Oil Company | Gasoline composition for reducing intake valve deposits in port fuel injected engines |
US5507843A (en) * | 1994-09-19 | 1996-04-16 | Shell Oil Company | Fuel compositions |
WO1996011999A2 (en) * | 1994-10-12 | 1996-04-25 | Exxon Chemical Patents Inc. | Lubricating oil mannich base dispersants derived from heavy polyamine |
US5512067A (en) * | 1995-05-22 | 1996-04-30 | Ethyl Corporation | Asymmetrical mannich base derivatives and the production and uses thereof |
US5514190A (en) * | 1994-12-08 | 1996-05-07 | Ethyl Corporation | Fuel compositions and additives therefor |
US5516342A (en) * | 1992-12-28 | 1996-05-14 | Chevron Chemical Company | Fuel additive compositions containing poly(oxyalkylene) hydroxyaromatic ethers and aliphatic amines |
US5538521A (en) * | 1993-12-23 | 1996-07-23 | Chevron Chemical Company | Fuel compositions containing polyalkyl and poly(oxyalkylene)aromatic esters |
US5540743A (en) * | 1994-12-30 | 1996-07-30 | Chevron Chemical Company | Polyalky and poly(oxyalkylene) benzyl amine esters and fuel compositions containing the same |
US5558683A (en) * | 1995-03-20 | 1996-09-24 | Ethyl Corporation | Mannich base derivatives, and the production and uses thereof |
US5599359A (en) * | 1995-12-29 | 1997-02-04 | Chevron Chemical Company | Polyalkylphenyl and polyalkyloxycarbonylphenyl hydroxybenzoates and fuel compositions containing the same |
US5628803A (en) * | 1995-12-29 | 1997-05-13 | Chevron Chemical Company | Polyalkylphenyl and polyalkyloxycarbonylphenyl amino and nitro benzoates and fuel compositions containing the same |
US5634951A (en) * | 1996-06-07 | 1997-06-03 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
EP0803515A2 (en) * | 1992-03-20 | 1997-10-29 | Chevron Chemical Company | Fuel additive compositions containing poly (oxyalkylene) amines and polyalkyl hydroxyaromatics |
US5693725A (en) * | 1995-08-29 | 1997-12-02 | Lifesource International, Ltd. | Crosslinked Mannich-Michael polycondensates |
US5697988A (en) * | 1991-11-18 | 1997-12-16 | Ethyl Corporation | Fuel compositions |
US5713966A (en) * | 1993-10-28 | 1998-02-03 | Chevron Chemical Company | Polyalkyl hydroxyaromatic esters and fuel compositions containing the same |
EP0831141A1 (en) * | 1996-09-05 | 1998-03-25 | BP Chemicals (Additives) Limited | Detergents for hydrocarbon fuels |
WO1998047989A1 (en) | 1997-04-21 | 1998-10-29 | Exxon Chemical Patents Inc. | Power transmission fluids containing alkyl phosphonates |
US5830244A (en) * | 1996-12-30 | 1998-11-03 | Chevron Chemical Company | Poly (oxyalkyene) benzyl amine ethers and fuel compositions containing the same |
US5855630A (en) * | 1994-09-19 | 1999-01-05 | Shell Oil Company | Fuel compositions |
US6039773A (en) * | 1997-12-22 | 2000-03-21 | Chevron Chemical Company Llc | Fuel compositions containing polyamines of polyalkyl aromatic esters |
US6048373A (en) * | 1998-11-30 | 2000-04-11 | Ethyl Corporation | Fuels compositions containing polybutenes of narrow molecular weight distribution |
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US6179885B1 (en) | 1999-06-22 | 2001-01-30 | The Lubrizol Corporation | Aromatic Mannich compound-containing composition and process for making same |
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